Ethyl dichloroacetate → HCID 23312114, compound

HRID 745795Notes

Reaction equation

HRID 745795 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9]([C:12]1[CH:13]=[C:14]([OH:20])[C:15]([OH:19])=[CH:16][C:17]=1[CH3:18])(=[O:11])=[O:10].C([O:23][C:24](=[O:28])[CH:25](Cl)Cl)C.C(=O)([O-])[O-].[K+].[K+]>COCCOC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9]([C:12]1[C:17]([CH3:18])=[CH:16][C:15]2[O:19][CH:25]([C:24]([OH:28])=[O:23])[O:20][C:14]=2[CH:13]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 10808Ethyl dichloroacetateHCID 11430Potassium CarbonateHCID 23312052HCID 23312052, compound

Product 1

HCID 23312114HCID 23312114, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

In a manner analogous to that described in Example 4, 21.3 g (64 mmol) of 4-(2,5-dichlorophenylsulphonyl)-5-methyl-1,2-benzenediol, 10.0 g (64 mmol) of dichloroacetic acid ethyl ester and 44.2 g (320 mmol) of potassium carbonate in 160 ml of 1,2-dimethoxyethane are boiled under reflux. After 18 hours, the reaction mixture is filtered and the solid filtration residue is washed twice with 1,2-dimethoxyethane. 44 g of fresh potassium carbonate and 10 g of dichloroacetic acid ethyl ester are added to the combined organic solutions and the whole is stirred for 5 minutes using a high-speed stirrer and boiled, while stirring normally, for a further 17 hours. Working up is carried out in a manner analogous to that described in Example 10. After drying carefully, 5-(2,5-dichlorophenylsulphonyl)-6-methyl-1,3-benzodioxole-2-carboxylic acid is obtained in the form of white crystals having a melting point of 155°-157° (from diisopropyl ether).

Workup

  1. temperatureunder reflux
  2. filtrationthe reaction mixture is filtered
  3. filtrationthe solid filtration residue
  4. washis washed twice with 1,2-dimethoxyethane
  5. addition44 g of fresh potassium carbonate and 10 g of dichloroacetic acid ethyl ester are added to the combined organic solutions
  6. stirringwhile stirring normally, for a further 17 hours
  7. customAfter drying carefully

Sources & evidence

ORD record
ord-8c4792a3143249b981082e9e9675ae36
Source dataset
uspto-grants-1986_07
Patent number
US04600709

Reaction notes

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